A theoretical study on the role of ortho, meta and para situation of different electron donating functional groups on the electronic structure and aromaticity of phenol molecule

Aromaticity is of fundamental importance to chemistry. In this paper, the role of ortho, meta and parasituation of different electron donating functional groups on the electronic structure and aromaticity of phenol moleculehave been investigated. The stability energy of each molecule have been considered. Results show that, the stabilityenergy of three isomers of each phenol derivative have not considerable differences. In NH2 and OCH3 functionalizedphenol the O-H bond length in ortho isomers are higher than in the other isomers. Simultaneously, in each case, the OCbond is shorter. About CH3 functionalized phenol there is not a meaningful difference between O-H and O-C bondlength in different isomers. In all considered derivatives the electronic charge on H atom in ortho isomer is more thantwo other isomers. Variation of NICS (1) and NICS (1)ZZ, calculated for ortho, meta and para isomers follow a similartrend. In the case of NH2 and CH3 substitution, the maximum aromaticity has been obtained when the ortho situationoccupied with functional group. On the other hand, para substitution of OCH3 functional group cause to maximize thearomaticity of phenol.

کلیدواژه ها:

substitution effect ، electron donating functional groups ، NICS